Bielschowskysin, a gorgonian-derived antiplasmodial diterpene with an unprecedented carbon skeleton

ORGN 518

Jeffrey Marrero, Abimael D. Rodríguez, Peter Baran, and Raphael Raptis. Department of Chemistry, University of Puerto Rico, PO Box 23346, San Juan, PR 00931-3346

Bielschowskysin (1) is a naturally occurring regular diterpene isolated from the Caribbean gorgonian octocoral Pseudopterogorgia kallos. Its highly oxygenated hexacyclic structure possesses several unusual stuctural features. In addition to having two cyclic hemiacetals, a g -lactone, and a tetrasubstituted cyclobutane moeities, bielschowskysin (1) is based on a previously undescribed tricyclo[9.3.0.02,10]tetradecane ring system whose structure was established through spectroscopic analysis and X-ray crystallographic analysis. Bielschowskysin (1) was shown to exhibit strong antimalarial activity against Plasmodium falciparum.

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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004